My Cousin, My Escort

That thought lingered like a seed buried deep in her brain for a few years. Eventually, it grew into posting nude photos on Reddit to see what the reaction would be. Then selling custom nudes to her followers. Then, finally, getting propositioned offline again.

It wasn't until 2017 that Cassie took money for real-life sex work and her first experience was about as boring as it gets. The guy was named Ed. He was a coworker at her day job in an auto insurance company and, while drunk one night, he offered her $300 to fuck. She turned him down. He wasn't that attractive and she wasn't interested.

But when he offered her $200 just to get topless and let him jerk off in front of her? Who could say no to such easy money?

He lasted five minutes. She didn't actually have to do anything.

Immediately, she was hooked.

The more Cassie thought about becoming an escort, the more it excited her. Sure, sex with random people you meet on Tinder or in a bar is fun but sex with a complete stranger? When it's also kind of against the law? There's something hot about that.

It took Cassie until she was 31 before she thought about seriously doing it. It took her another 10 months to put up her first ad but, once she did, there was no turning back. On her best nights, she got paid to sit and listen to guys complain about their lives. On her worst, she had to fuck some unattractive mid-level white collar douchebag who could only last, maybe, ten minutes.

That was three years ago. And though she doesn't take a lot of clients, Cassie's built a steady customer base and only advertises occasionally when the need arises. She still has her insurance job but it's mostly to keep appearances for her friends and family. The sex work was the real money-maker and, if she played her cards right, it would be the reason she'd retire decades before she would have otherwise.

Sex work is also how she started talking to Roger and tonight, she was going to meet him and they were going to have sex. It was going to be quick. It was going to be easy. And she was going to be $1,200 richer. Or ... that's what she told herself as she headed out the door to his hotel room.

=====

The red glow of the hotel alarm clock read 7:59 p.m. Tony knew his date would be there momentarily. That still didn't prepare him for when the knock actually came.

* knock knock *

"Oh God," he thought. "Here we go."

Tony had played this scenario out in his head a million times and he knew how he wanted to approach it but, it was still so different now that this was real life.

In porn, this is the moment where the viewer knows things are about to go down. The confident man opens the door, the escort comes in, they talk details and then the sex begins.

In real life, it's so much more nerve-racking.

Tony looked at the clock one last time, took a deep breath and made his way into the bathroom right before the knock came. The way the room was laid out, it was the best way for him to make his first impression.

Tony had booked a nice little suite on the ground floor of a pretty busy hotel on International Drive, a popular spot for tourists going to and coming from Disney, which was 10 or so minutes down the road.

He chose the spot for its quick access to the interstate, because it was popular enough that people coming in and out at all hours wouldn't seem odd and because he knew his wife hated tourists in her state enough that she'd NEVER accidentally discover him there. If you live in Florida, the last thing you want to do is deal with the zombie-like herds who come to the state, stuff their fat asses and triple chins into the same three chain restaurants and leave proclaiming it the best vacation spot in the world.

The suite was surprisingly bigger than he expected for the price and was organized in an 'L' shape with a kitchen area and a full-size fridge greeting visitors as they first walked in.

Tony used the fridge to store a few Gatorades for himself, a six pack of Coke, a couple of bottles of water and a bottle of champagne in case Alyssa was thirsty. He tried to cover all his bases with the beverages.

The room also had two tall chairs, a full working kitchen with oven and a sink and a beautiful marble counter. On the left of the kitchen was a bathroom, which had a small, enclosed shower, a large mirror over the sink and a full-size mirror on the wall.

It was the perfect suite for the tourist clients who usually booked it and, inside, there was a small living room space with a dark brown couch, a beige chair that was deceptively comfortable, a small wooden table to rest snacks on and two end tables with white lamps on them.

The living room led right into an open-area bedroom, which came equipped with a King size bed and a couple more end tables and lamps but was otherwise about as basic as could be expected.

Tony chose this room intentionally as it had everything he needed to play out the fantasy he'd had in his mind most of his adult life. He mentally envisioned this hundreds of times.

The plan was to leave the door slightly ajar, hear his companion knock, tell her to let herself in and seconds later stroll out of the bathroom casually to seem as confident as possible. He wanted to look like someone who had done this before and not a nervous rookie.

Now that this moment was here, however, he was anything but confident.

He heard her knock. His heart beat increased.

"Come in," he said from the bathroom, grabbing a paper towel to wipe the sweat from his head one last time.

The door slowly opened and Tony took a look in the mirror over the sink one last time. He took a deep breath, gave himself a mini pep talk and prepared to walk out. Then he heard her first words. She was here. For real.

"Hello?," Cassie said to an empty room. "It's Alyssa. I'm looking for Roger?"

Tony walked toward the bathroom door and headed to the voice that called out his made-up name. The moment he saw her for the first time, he couldn't help himself. Without thinking and before he could even process what he was witnessing, the words fell out of his mouth.

"Oh fuck."

=====

Five minutes earlier, Cassie had arrived to the hotel.

As she entered the parking lot, she went through her usual checklist in her head. It was a simple ritual but one that ensured her protection and allowed her to get into what she called her "hooker mentality."

It's an important mindset, especially for someone like Cassie who likes to keep her personal and professional lives separate. By only getting in "hooker mentality" when she was getting ready to meet a client, Cassie was able to treat that part of her life like a character she was playing. It made it much easier to distinguish between the person who went to work every day and seemed to be your average American business woman as opposed to the person who sucked dick and fucked for cash.

Cassie drove past the room Roger said he was in twice, scanned around for anything that seemed suspicious and circled back to the front of the hotel to park. No cameras. No suspicious vehicles. So far so good.

Cassie chose the closest spot next to the exit when she parked her car. The good news was, a spot like this made her feel much safer in case she had to make a run for it and return for the car later. The bad news was it made the walk to her clients' room longer and left her more time to think and get nervous. Even in her third year doing this, butterflies were inevitable.

A few minutes before she arrived to the hotel, Cassie sent a text to her friend Jenny to let her know exactly where she would be if something happened, roughly how long they'd be and when to expect an "all safe" text later that night with a codeword only the two of them knew. That last part might have been a bit much but, hey, it's better to be safe than sorry.

Cassie had only ever been late with that "all safe" text once and that was because she lost track of time after a particularly great session with a client who paid her $3,000 just to eat her pussy. Too bad every client couldn't be like that.

Still, it's not the kind of mistake to make often. Not when you're meeting strangers in private hotel rooms and doing your best to keep it under the radar from the people in your day-to-day life.

Cassie was meticulous in her planning of these sessions and that's why she only had a handful that weren't great.

It started with her appearance. She arrived at every client booking wearing run-down mom jeans and a loose-fitting t-shirt. Her hair was never overly done. Her makeup was simple but effective. It was much easier to blend in that way and she could fit whatever sexy lingerie she needed to wear and any hair and makeup products for last minute or needier clients in the travel-sized luggage case that she always had by her side for these types of dates

It's especially easy to blend in at a place like the hotel Roger chose, one that serves tons of tourists who don't know anyone else or pay attention to much beyond their own vacations and itineraries.

It helped, of course, that most of Cassie's clients weren't looking for the stereotypical "escort," that people might see on TV. The ones wearing cliche high heeled shoes that would make walking more than ten feet impossible. The ones who have their tits out the minute they get ready to meet a client. The ones whose appearance practically screams "pay me to fuck."

If Cassie were escorting in Vegas, which she ruled out pretty early on in her career, she might have approached the job differently. Maybe she'd look more like the stereotype.

Serving clients in tourist-friendly Orlando, though, was much easier than Vegas and it allowed her to stay close to home. That was important. She didn't to live too far away and have to alter her day-to-day life with friends and family. But she wanted to be far enough away that the risk of running into someone she knew was pretty low.

Orlando offered the perfect balance. After all, if you live in Florida, the last thing you want to deal with are the vacationing tourists who ruin everything.

Cassie did live the escort lifestyle in other ways. She had all the sexy clothes expected from a woman in her position and more sex toys than she ever thought she'd own but most of that stuff stays tucked away in boxes in her closet unless needed for a client.

The clients rarely asked for them but when they did? She'd happily oblige ... but not until she got to their room and dressed up in the bathroom on site. Safety was always the top priority and keeping her appearance mundane until it was time to get to work kept her off the radar of those who might object to seeing a paid sex worker on their property.

Roger's request for her outfit played right into her comfort zone. He wanted to see her in all black, with black stockings on and a garter belt. He also asked her to bring a sexy black bra and thong and she had that all in her bag. What's more, he wanted her to wear normal clothes on top of that and start their session by stripping for him before giving him a lap dance.

It was about as basic a request as you can get in this line of work, Cassie thought, and given her experience with those types of customers, they usually popped seconds into the session so she figured it wouldn't be a particularly long night. Still, she DVR'd her favorite show that night just in case things went the full hour she had been paid for.

Cassie hadn't seen a photo of Roger prior to her visit but she expected him to be like the majority of her clients. Slightly chubby, balding, mid 40s and completely awful at pleasing a woman who wasn't getting paid.

She checked her face in the rear view mirror of her car one last time before leaving. Her eyebrows looked great, there was nothing in her teeth and she was ready to go.

It took her a few moments to reach Roger's hotel room and, when she did, she noticed the door was slightly ajar, with the slide-lock that provided extra security propped in between the door and the hinge to allow guests to come in at ease.

Still, she knocked. It was the professional thing to do.

"Come in" she heard a voice say.

Cassie opened the door and saw a pretty nice, but empty, hotel room.

"Hello?," she said to an empty room. "It's Alyssa. I'm looking for Roger?"

She saw the bathroom door to her left was open and knew her soon-to-be client was about to come out. The moment she saw him, she couldn't help herself. In an instant, her "hooker mentality" was shattered, her mouth was opened and the words poured out.

"Oh shit."

=====

Two profanities. Uttered a split second apart. From two people who both knew why they were in this hotel room but couldn't work up the courage to talk about it.

It had only been about 30 seconds since Tony walked out of an empty bathroom and ran into his cousin Cassie but those seconds felt like years.

Neither knew what to say next. What could they say? They were both busted. Their secrets that they had spent so much time and effort to keep, gone.

Tony spoke first. Not because he wanted to but because he had to.

"What the fuck?" he asked.

Silence.

"What, what, what are you ... why are you ... huh?" he stumbled out.

Cassie wanted to cry. She didn't even hear Tony's words.

It's not that she thought she was too smart to get outed as an escort. That was part of the job. But she didn't expect it to be a member of her own God damn family who caught her in the act.

He must have known it was her. He must have been able to tell from the ad. Or the email address. Or the something. Anything. It didn't make sense. She was so careful. She made sure to get his name and his referen...

Fuck.

In an instant, Cassie thought back to all the moments she defied her usual screening process in the lead up to this encounter. How could she be so stupid.? Worse, what the hell was she supposed to say now? She was busted. One hundred percent.

"What are you doing here?" Tony asked again, this time more sternly.

Wait.

That's it.

Cassie finally figured it out.

"Hold on. YOU? YOU ordered an escort?" she couldn't stop herself from asking that question in a way that sounded like she was shaming him. In reality, that wasn't her intent but she didn't know that. She was scared and just trying to make sense of this entire situation.

"YOU'RE an escort?" Tony asked back.

Neither spoke for what, again, seemed like forever.

"I've got to ..." Cassie stuttered. "I've got to get out of here."

Before Tony could process what just happened, Cassie turned around and bolted out of the room. It took the sound of the door bouncing hard off the hinge to shake Tony from his frozen state.

He didn't say a word. He walked over to the couch in his room and sat down on it, awe-struck at the sheer stupidity required to order your own fucking cousin as an escort.

If he wasn't so scared about what would happen next, he would have found this whole scenario hilarious. In reality, it was pretty funny. But not right now.

Right now he wanted to throw up.

=====

The moment Cassie finally processed what she was going through, she knew she had to get the hell out of this hotel room.

Grabbing the luggage case she placed on the floor when she walked in, she turned away from her cousin, grabbed the handle of his hotel room door and flew out of that room. She could hear the door bounce on her way out. Cassie bolted for her car. She walked faster and with more purpose than ever before. She. Can. Not. Have this discussion. Not with him. Not with family.

He wouldn't understand why she was doing what she was doing. It's one thing to idolize the classic Hollywood hooker stereotype that everyone who does sex work is damaged or looking for love but that's really not her. She does it because she wants to and when you're trading sex for money, there are people who get it and people who don't. No way would HE get it.

Speaking of ... what in the fuck was he even doing there? Tony was a normal guy and in a happy marriage. Was he really cheating on Kayla? He's the LAST person she would've expected that from.

"I've got to get home," she thought.

Cassie made it all the way to her car, tossed her luggage back into her trunk and turned the key into her ignition before she realized she couldn't go anywhere. She was stuck.

"Shit."

She might have wanted to leave. Every bit of her instinct was that she needed to leave. But she couldn't. She couldn't leave it like that.

She sat in her driver's side seat with the ignition turned on and the seatbelt warning beeping for at least five minutes before she knew what she needed to do.

She got out of the car.

=====

What do you do when your family finds out you tried to pick up an escort?

Tony sat on the dark brown couch in his hotel room wondering that and trying to play out how that talk would go with his mother, sister, brother and inevitably his wife.

Now, his wife wasn't likely to be upset because they did have an understanding but the entire point of their agreement was to not have it come up in their day-to-day lives. Trying to hire your cousin to have sex with you for money was the exact opposite of that.

"How was I supposed to know?" he thought.

Thinking back, there really was no way he would've known it was Cassie in those ads. For one thing -- and, yes, he knew this is a stupid thing to say -- she wasn't using her real name.

For another, none of her photos had shown her face.

Frankly, he'd never thought of his cousin in a sexual way before. How was he supposed to know that's what she did for work? He wasn't all that close to her, really. Sure, they saw each other at family gatherings and would chat for a bit but she's the LAST person he would picture doing sex work.

Oh God.

She's a hooker.

She's a fucking hooker.

Tony tried to wrap his head around the decisions that had led to this moment but it was Cassie's that concerned him the most. How long had she been doing this? Did she really sleep with strangers for cash? How could she do that to herself? That's so disgusting and shameful.

The irony that Tony hired her for the very thing he wanted to mentally shame her for wasn't lost on him.

"You know what?" he thought. "Who the hell am I to judge?'

Cassie might have a million reasons she does what she does but exactly zero of them were Tony's business.

After all, if she really cared what he thought of her chosen field, she would have told him about it long before she walked into his hotel room. And judging by the quick way she stormed off, it was clear she wasn't interested in having that discussion now.

Would they ever talk about? It's hard to tell. That's just not something easy to bring up in conversation. Maybe in a few years they'll be able to laugh and joke about it but, even then, that sounded delusional.

What was more likely, he thought, was that this would make every family gathering they were both at incredibly awkward for the rest of their lives. No way would she want to bring it up, he thought. And it's not like he'd be eager to do so either.

It took a little while but the fear Tony felt in the immediate moments of walking in on Cassie eventually faded. In its place came a rush of embarrassment and he felt like an idiot.

"Only a dumbass would try to hire his cousin to be his escort." he thought, cupping his forehead in his hands and rubbing his temple.

And he'd already paid her. In advance. Say goodbye to that money.

What a stupid decision. What a dumb night. Fuck this.

It took a few minutes for Tony to get over his stupidity but when he finally accepted he'd have to cut his losses, he felt ready to get off the couch and pack his stuff for an unexpected early checkout.

The moment he got up, though, he heard the one sound in the world he really wasn't prepared for.